It was not a good night for candidates bankrolled by GOP megadonor Rex Sinquefield.

The retired investor from St. Louis was funding a slate of candidates in the Republican primary to the tune of nearly $11 million. And as the results rolled in Tuesday night, it became clear each of his candidates lost big.

Catherine Hanaway took more than $4.5 million from Sinquefield and his various political action committees and ended up finishing fourth in a four-way gubernatorial primary.

Kurt Schaefer got $3.5 million from Sinquefield and was defeated by University of Missouri law professor Josh Hawley by nearly 30 points in the attorney general primary.

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Bev Randles got $2.5 million of Sinquefield donations but still lost to Mike Parson in the lieutenant governor primary.

Will Kraus, who received $120,000 from Sinquefield, was soundly defeated by Jay Ashcroft in the race for secretary of state.

The only statewide candidate to receive significant support from Sinquefield who will be on the ballot this fall is Eric Schmitt, who was unopposed in the Republican primary for state treasurer.

In a state with no limits on campaign contributions, Sinquefield far outpaces any other donor in the size and scope of his spending. Since 2008, when the legislature repealed voter-imposed contribution limits, Sinquefield has donated more than $45 million to candidates and campaigns in Missouri.

So does Sinquefield’s string of defeats mean money has less of an impact on campaigns than many believe? Not so fast, say political observers.

“His money might not be able to buy campaigns in Missouri, but other people’s money certainly made a difference,” said Dave Robertson, a professor of political science at the University of Missouri-St. Louis. “This was a big money election, and candidates had to spend a lot of money to keep up with each other to get their name and message out.”

Hanaway was bankrolled by Sinquefield, but her Republican rivals for the nomination weren’t struggling for cash. Retired businessman John Brunner pumped millions of his own money into the campaign, and Lt. Gov. Peter Kinder had the support of Joplin businessman David Humphreys, who along with his sister gave Kinder $1.5 million.

The winner of the Republican primary for governor, former Navy SEAL Eric Greitens, raked in huge campaign contributions, including a $1.9 million check from a Washington, D.C.-based super PAC called SEALS for Truth. Additionally, he scored six-figure contributions from out-of-state donors like Sheldon Adelson, the Las Vegas casino mogul who gave Greitens $200,000 last month.

As for Humphreys, he had a big night Tuesday. He focused much of his spending on legislative races, helping fund anti-labor-union candidates who were challenging Republican incumbents around the state. His favored candidates managed to knock off two incumbent Republicans in the Kansas City area Tuesday night.

Sinquefield’s deep pockets promise a seemingly endless fight over his pet causes — revamping the state’s education system and eliminating the Missouri income tax. But his record of electoral success isn’t sparkling.

His biggest win came in 2010, when he spent spent $11 million on a successful ballot measure that forced St. Louis and Kansas City to hold votes on their local earnings tax every five years. Earlier this year, he spent more than $2 million trying to persuade voters to repeal the tax, and Kansas City voted overwhelmingly to keep it.

He helped fund primary challengers to Republican lawmakers who voted against a tax-cut bill in 2014, and in each race his favored candidate lost. Yet the following legislative session, a pared-down version of the tax cut was passed over the veto of Gov. Jay Nixon — a big win for Sinquefield.

A spokesman for Sinquefield didn’t respond to a request for comment, but he told the St. Louis Post-Dispatch the fact that candidates who support tax cuts were successful Tuesday night is evidence that Sinquefield is having an impact on Missouri politics. And the megadonor has no intention of paring down his contributions heading into the fall campaign, even if his initial candidates weren’t victorious.

“I think everybody is ready to move forward, encouraged by the fact that the people who campaigned for tax cuts and who want to lower the price of work are still running,” said Sinquefield spokesman Travis Brown. “It’s not over until Nov. 8.”

Robynn Kuhlmann, assistant professor of political science at the University of Central Missouri, said she expects the big money to continue to pour in to Missouri campaigns through the fall. And the negative tone of the primary is likely just a preview to what voters should expect this fall, she said.

“If they can do that to members of their own party,” she said, “they’ll certainly do it to members of the opposing party.”